Method for improving the foaming properties of cleansing and/or foaming formulations for topical use

ABSTRACT

Methods for improving the foaming properties of cleansing and foaming formulations for topical use are presented. The methods comprise including in the formulation an effective amount of a polyol glycoside or a mixture of polyol glycosides of formula (I) R 1 —O-(G) x -H, in which x is a decimal number between 1 and 5, G is a reducing sugar and R 1  is a radical of formula (A) —CH 2 —(CHOH) n —CH 2 —OH, in which n is an integer equal to 2, 3 or 4, or R 1  is a radical of the formula (B) —(CH 2 —CHOH—CH 2 —O) m —H, in which m is an integer equal to 1, 2 or 3. Compositions containing compounds of formula (I) and methods of preparing the compositions are also presented. The methods and compositions can be applied to cosmetics and dermapharmaceuticals.

This application is a divisional application of application Ser. No.12/298,862 filed Oct. 28, 2008, now U.S. Pat. No. 7,915,208, which is a371 National Stage application of PCT/FR07/51119 filed Apr. 16, 2007,which claims priority to French Application No. 06 51519 filed on Apr.28, 2006. The entire contents of each of the above-identifiedapplications are hereby incorporated by reference.

FIELD OF THE INVENTION

The present invention relates to a novel process for improving thefoaming properties of cleansing and/or foaming formulations, to novelcompositions and to processes for preparing them, and also to thepreparation of formulations for topical use containing them.

The invention preferentially finds application in the cosmetic anddermocosmetic fields, in the dermopharmaceutical and pharmaceuticalfields, but also in the field of the textile industry, for example fortreating synthetic or natural, woven or knitted textile fibers, oralternatively in the field of the paper industry, for example for themanufacture of paper for sanitary or domestic use.

BACKGROUND OF THE INVENTION

The development of cleansing formulations for the face, the body and thehair, and in general body and hair hygiene products, presented in theform of shampoos, lotions, gels or liquid soaps requires the formationof foam during application to the part of the body to be cleansed. Thisconcern is particularly important since, in the eyes of the consumer,the creation of foam constitutes one of the proofs of the cleansingefficacy of these formulations. In the development of cleansingformulations for body and hair hygiene, the volume of foam generated bythe formulation, and also its stability and the sensory properties ofsaid foam, constitute an important criterion for the commercial successof the products proposed to consumers. Thus, the search for formulationsthat generate a foam of good quality is also broadened to all washingproducts for the body, shower gels and bubble baths.

Several categories of surfactant are used for the preparation offormulations for cleansing purposes: cationic, anionic, amphoteric ornonionic surfactants.

Anionic surfactants, such as sulfated anionic surfactants or surfactantsof the alkylcarboxylate family, constitute a class of surfactants thatis frequently used on account of their good foaming properties. Thesesurfactants are reputed for their good cleansing power, and may alsoproduce an airy foam whose feel is not considered by consumers to beunpleasant. However, these surfactants have the drawback of beingsensitive to the degree of water hardness and to the presence of greasysoiling, which consequently induces a reduction in the volume of foaminitially generated by these formulations, but above all a reduction inthe stability over time of this volume of foam.

To reduce the magnitude of these phenomena, without, however,eliminating them altogether, it is preferred to use alkyl ether sulfatesrather than alkyl sulfates. Another solution, which again is onlypartially satisfactory, consists in using nonionic surfactants, such asalkylpolyglycosides, for instance decyl polyglucoside or capryl/caprylylpolyglucoside. On account of their nonionic structure, these surfactantsare compatible with any other type of surfactant, of additive and ofactive agent with cosmetic properties, irrespective of their anionic,cationic or nonionic nature. They especially show excellentcompatibility with the quaternary ammonium derivatives used either fortheir bactericidal properties, or for their hair-conditioning effect.Furthermore, alkylpolyglycosides are known for their excellent capacityto form an abundant, stable foam, independently of the pH of theformulation, which foam is insensitive to the degree of water hardnessand to the presence of greasy soiling. However, alkylpolyglycosidesproduce a foam that has mediocre sensory characteristics, reflected by acoarse foam feel, which induces during the rinsing phase a gratingeffect that consumers find particularly unpleasant, both on the skin andon the hair.

To attempt to overcome these drawbacks, it is necessary either to use asmall dose of alkylpolyglycosides in the cleansing formulations, or tocombine the alkylpolyglycosides with feel modifiers, for instancewater-soluble fatty phases such as silicone fatty phases or esters.Although such combinations make it possible to improve the sensoryproperties of the foam, they however have the consequence of verysignificantly reducing the volume of foam formed during use by theconsumer, and, in certain cases, of impairing the foam stability overtime.

The inventors have thus sought to develop a novel solution for improvingthe foaming properties of cosmetic, dermocosmetic, dermopharmaceuticalor pharmaceutical formulations.

BRIEF DESCRIPTION OF THE INVENTION

Consequently, according to a first aspect, a subject of the invention isa process for improving the foaming properties of a cleansing and/ordetergent formulation for topical use, characterized in that aneffective amount of a compound of formula (I):R₁—O-(G)_(x)-H  (I)

in which:

-   -   x represents a decimal number between 1 and 5,    -   G represents a reducing sugar residue, and    -   R₁ represents a monovalent radical of formula (A):        —CH₂—(CHOH)_(n)—CH₂—OH  (A)

in which n is an integer equal to 2, 3 or 4, or alternatively

-   -   R₁ represents a monovalent radical of formula (B):        —(CH₂—CHOH—CH₂—O)_(m)H  (B)

in which m is an integer equal to 1, 2 or 3,

-   -   or a mixture of compounds of formula (I), is incorporated into        said composition.

DETAILED DESCRIPTION OF THE INVENTION

In the definition of formula (I) as defined previously, x is a decimalnumber that represents the mean degree of polymerization of the residueG. When x is an integer, (G)x is the polymer residue of rank x of theresidue G. When x is a decimal number, formula (I) represents a mixtureof compounds:a ₁R₁—O-G-H+a ₂R₁—O-(G)₂-H+a ₃R₁—O-(G)₃-H+ . . . +a _(q)

R₁—O-(G)_(q)-H with q representing an integer between 1 and 10 and inthe mole proportions a₁, a₂, a₃, . . . a_(q) such that:

${{\sum\limits_{q - 10}^{q - 1}\; a_{q}} = 1};$ a₁ > 0

According to another particular aspect of the present invention, in thedefinition of the compounds of formula (I), x is between 1.05 and 5, andmore particularly between 1.05 and 2.

The term “effective amount” denotes, in the definition of the process asdefined above, an amount such that the final formulation obtained bysaid process:

-   -   generates a volume of foam of greater than or equal to 300 cm³,        30 seconds after its formation, according to the operating        conditions of the Ross-Miles test derived from standard ISO 696        and AFNOR NFT 73-404, the protocol of which is described in        paragraph B.1.2 of the experimental section of the present        description;    -   shows a foam stability of greater than 90%, 5 minutes after its        formation, according to the operating conditions of the        Ross-Miles test.

According to one particular mode of the process as defined above, theterm “effective amount of compound of formula (I)” denotes a massproportion of from 0.1% to 20%, most particularly from 0.5% to 10% andeven more particularly from 1% to 5% of the final formulation.

The term “for topical use” used in the definition of the process asdefined above means that said composition is used by application to theskin, the hair, the scalp or mucous membranes, whether it is a matter ofa direct application in the case of a cosmetic, dermocosmetic,dermopharmaceutical or pharmaceutical composition, or of an indirectapplication, for example in the case of a body hygiene product in theform of a textile or paper wipe or of sanitary products intended to comeinto contact with the skin or mucous membranes.

The term “reducing sugar” denotes, in the definition of formula (I) ofthe compound used in the process as defined above, saccharidederivatives that do not have in their structure a glycoside bondestablished between an anomeric carbon and the oxygen of an acetalgroup, as defined in the reference text: “Biochemistry”, DanielVoet/Judith G. Voet, p. 250, John Wiley & Sons, 1990.

The oligomeric structure (G)_(x) may be in any isomeric form, whether itis optical isomerism, geometrical isomerism or positional isomerism; itmay also represent a mixture of isomers.

In formula (I) as defined above, the group R₁—O— is bonded to G via theanomeric carbon of the saccharide residue, so as to form an acetalfunction.

According to another particular aspect of the process as defined above,in formula (I), G represents a reducing sugar residue chosen fromglucose, dextrose, sucrose, fructose, idose, gulose, galactose, maltose,isomaltose, maltotriose, lactose, cellobiose, mannose, ribose, xylose,arabinose, lyxose, allose, altrose, dextran and talose, and moreparticularly a reducing sugar chosen from glucose, xylose and arabinose.

According to one particular aspect of the present invention, one subjectthereof is a process as defined previously, in which the cleansingand/or detergent formulation for topical use comprises at least onefoaming and/or detergent surfactant.

The term “foaming and/or detergent surfactant” denotes the topicallyacceptable anionic, cationic, amphoteric or nonionic surfactants usuallyused in this field of activity.

Among the anionic surfactants that may be combined with these compoundsand with these formulations, mention will be made particularly of alkalimetal salts, alkaline-earth metal salts, ammonium salts, amine salts andamino alcohol salts of the following compounds: alkyl ether sulfates,alkyl sulfates, alkylamido ether sulfates, alkylaryl polyether sulfates,monoglyceride sulfates, α-olefin sulfonates, paraffin sulfonates, alkylphosphates, alkyl ether phosphates, alkylsulfonates,alkylamidesulfonates, alkylaryl-sulfonates, alkylcarboxylates,alkylsulfosuccinates, alkyl ether sulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, alkylsarcosinates,acylisethionates, N-acyltaurates and acyllactylates. Among the anionicsurfactants, mention will also be made of lipoamino acids, lipoproteins,lipopeptides, lipoprotein derivatives, protein derivatives, fatty acidsalts, and salts of optionally hydrogenated coconut oil acids.

Among the amphoteric surfactants that may be combined with thesecompounds and with these formulations, mention will be made particularlyof alkylbetaines, alkylamidobetaines, sultaines,alkylamidoalkylsulfo-betaines, imidazoline derivatives, phosphobetaines,amphopolyacetates and amphopropionates.

Among the cationic surfactants that may be combined with these compoundsand with these formulations, mention will be made particularly ofquaternary ammonium derivatives.

Among the nonionic surfactants that may be combined with these compoundsand with these formulations, mention will be made particularly ofalkylpolyglycosides, castor oil derivatives, polysorbates, coconutamides, N-alkylamines and amine oxides.

Among the foaming and/or detergent surfactants mentioned above, whichare anionic surfactants, there are more particularly the compounds offormula (II):[R₂—O—(CH₂—CH₂—O)_(p)SO₃]_(r)X  (II)

in which:

-   -   R₂ represents a saturated or unsaturated, linear or branched        aliphatic hydrocarbon-based radical containing from 6 to 22        carbon atoms,    -   represents a decimal number between 1 and 10 and preferably        between 2 and 4,    -   r is an integer equal to 1 or 2, and    -   X represents the cation of an alkali metal or of an        alkaline-earth metal, the ammonium ion, the hydroxyethylammonium        ion or the tris(hydroxyethyl)-ammonium ion.

In formula (II) as defined above, X represents, for example, sodium,magnesium or ammonium.

Among the foaming and/or detergent surfactants mentioned above, whichare nonionic surfactants, there are more particularly the compounds offormula (III):R₃—O—(S)_(y)—H  (III)

in which:

-   -   y represents a decimal number between 1 and 5,    -   S represents a reducing sugar residue, and    -   R₃ represents a linear or branched, saturated or unsaturated        alkyl radical containing from 8 to 16 carbon atoms and        preferably from 8 to 14 carbon atoms.

In the definition of formula (III) as defined previously, y is a decimalnumber that represents the mean degree of polymerization of the residueS. When y is an integer, (S)_(y) is the polymer residue of rank y of theresidue S; when y is a decimal number, formula (III) represents amixture of compounds:a ₁R₃—O—S—H+a ₂R₃—O—(S)₂—H+a ₃R₃—O—(S)₃—H+ . . . +a _(q)

R₃—O—(S)_(q)—H with q representing an integer between 1 and 10 and inthe mole proportions a₁, a₂, a₃, . . . a_(q) such that:

${{\sum\limits_{q - 10}^{q - 1}\; a_{q}} = 1};$ a₁ > 0

According to another particular aspect of the present invention, in thedefinition of the compounds of formula (III), y is between 1.05 and 5and more particularly between 1.05 and 2.

In formula (III) as defined above, R₃ represents, for example, ann-octyl radical, an n-decyl radical, an n-dodecyl radical or ann-tetradecyl radical.

The term “reducing sugar” denotes, in the definition of formula (III) ofthe compound used in the process as defined above, saccharidederivatives that do not have in their structure a glycoside bondestablished between an anomeric carbon and the oxygen of an acetalgroup, as defined in the reference text: “Biochemistry”, DanielVoet/Judith G. Voet, p. 250, John Wiley & Sons, 1990. The oligomericstructure (S)_(y) may be in any isomeric form, whether it is opticalisomerism, geometrical isomerism or positional isomerism; it may alsorepresent a mixture of isomers.

In formula (III) as defined above, the group R₃—O— is bonded to S viathe anomeric carbon of the saccharide residue, so as to form an acetalfunction.

According to another particular aspect of the process as definedpreviously, the mass ratio of compounds of formula (I) to foaming and/ordetergent surfactants present in said composition for topical use isbetween 1/30 and 10/1 and more particularly between 1/30 and 1/1.

According to a second aspect, a subject of the invention is acomposition (C) comprising, per 100% of its mass:

-   -   from 97% to 40% by mass of a compound of formula (III):        R₃—O—(S)_(y)—H  (III)

in which:

-   -   y represents a decimal number between 1 and 5,    -   S represents a reducing sugar residue, and    -   R₃ represents a linear or branched, saturated or unsaturated        alkyl radical containing from 8 to 16 carbon atoms and        preferably from 8 to 14 carbon atoms, or a mixture of compounds        of formula (III);

from 1% to 25% by mass of a compound of formula (I):R₁—O-(G)_(x)-H  (I)

in which:

-   -   x represents a decimal number between 1 and 5,    -   G represents a reducing sugar residue, and    -   R₁ represents a monovalent radical of formula (A):        —CH₂—(CHOH)_(n)—CH₂—OH  (A)

in which n is an integer equal to 2, 3 or 4, or alternatively

-   -   R₁ represents a monovalent radical of formula (B):        —(CH₂—CHOH—CH₂—O)_(m)—H  (B)

in which m is an integer equal to 1, 2 or 3, or a mixture of compoundsof formula (I); and up to 50% by mass of a topically acceptable solvent.

In the context of the present invention, the term “topically acceptablesolvent” denotes solvents known to those skilled in the art that may beapplied to human and/or animal skin, to the scalp and to mucousmembranes.

According to a first particular aspect of the composition (C), informula (I), G represents a reducing sugar residue chosen from glucose,xylose and arabinose.

According to a second particular aspect of composition (C), in formula(I), R₁ represents a monovalent radical of formula (A) for which n isequal to 2 or 3, or a monovalent radical of formula (B) for which m isequal to 1 or 2.

According to a third particular aspect of composition (C), in formula(III), S represents a reducing sugar residue chosen from glucose, xyloseand arabinose.

According to a fourth particular aspect of composition (C), in formula(III), R₃ represents a radical chosen from n-octyl, n-decyl, n-dodecyl,n-tetradecyl and n-hexadecyl radicals.

The topically acceptable solvent is more particularly chosen from one ormore components of a group constituted by water, glycols, polyols,alcohols, alkoxylated polyols and glycol ethers.

In the context of the present invention, the topically acceptablesolvents are most particularly chosen from one or more components of agroup constituted by water, ethanol, isopropanol, butylene glycol,hexylene glycol, caprylyl glycol or 1,2-octanediol, pentylene glycol or1,2-pentanediol, ethylhexylglycerol or octoxyglycerol, glycerol,diglycerol, triglycerol, erythritol, xylitol, sorbitol, butyldiglycol,polyethylene glycols with a molecular weight of between 200 g·mol⁻¹ and8000 g·mol⁻¹, monopropylene glycol, dipropylene glycol, butyldiglycoland 2-methyl-1,3-propanediol.

Advantageously, the abovementioned topically acceptable solvent ischosen from water and one or more components of the group of polyolsconstituted by xylitol, erythritol, sorbitol, glycerol and diglycerol.

The compounds of formula (III) or the mixtures of compounds of formula(III), the compounds of formula (I) or the mixtures of compounds offormula (I) and the topically acceptable solvent may be incorporatedinto the cosmetic formulation for topical use separately or in the formof a composition (C) that is the subject of the invention. Moreover,according to one or more routes for preparing the compounds of formula(I) or mixtures of compounds of formula (I), which consists in reactinga reducing sugar G with a polyol of formula (A1):HO—CH₂—(CHOH)_(n)—CH₂—OH  (A1)

in which n is an integer equal to 2, 3 or 4 and/or of formula (B1):HO—(CH₂—CHOH—CH₂—O)_(m)—H  (B1)

in which m is an integer equal to 1, 2 or 3, the amount of unreactedpolyol, when this has been selected from one or more components of thegroup defined previously, may constitute all or part of the topicallyacceptable solvent. In this case, the compounds of formula (I) or themixtures of compounds of formula (I) and the topically acceptablesolvent are incorporated into the cosmetic formulation for topical useconcomitantly and the compounds of formula (III) may be incorporated ina subsequent step.

According to the processes used for preparing composition (C) accordingto the invention, (C) may residually comprise secondary compoundsresulting from the preparation of the compounds of formula (I), forinstance the polyols of formula (A1) or the polyols of formula (B1) intheir dehydrated forms. Composition (C) cannot comprise more than 10% ofthese secondary compounds.

Composition (C) that is the subject of the invention may be obtained byvarious routes:

A first synthetic route consists in a first step (a) in introducing acompound of formula (I) or a mixture of compounds of formula (I) and acompound of formula (III) or a mixture of compounds of formula (III)into a reactor at a controlled mass ratio, and in subjecting thismixture to efficient mechanical stirring, under temperature conditionsthat ensure the homogeneity of the mixture, preferentially between 20°C. and 90° C. If necessary, a second step (b) consists in introducing atopically acceptable solvent as defined previously into the mixtureobtained during step (a), and in continuing the stirring until ahomogeneous composition is obtained.

A second synthetic route for composition (C) according to the inventionconsists in synthesizing during a first step (a1) the compound offormula (I) or the mixture of compounds of formula (I) by introducing areducing sugar and a polyol of formula (A1) or (B1), for instanceerythritol, xylitol, glycerol, diglycerol, triglycerol or sorbitol, intoa reactor, at a controlled stoichiometric ratio, and in subjecting thismixture to an acetalization reaction under predetermined temperature andpartial vacuum conditions in the presence of an acidic catalytic system.The components of this acidic catalytic system will generally be chosenfrom sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid,hypophosphorous acid, methanesulfonic acid, para-toluenesulfonic acid,trifluoromethanesulfonic acid and acidic ion-exchange resins. Usually,the acetalization reaction will be performed at a temperature of from 70to 130° C., under a vacuum of from 300 to 20×10² Pa (300 to 20 m bar).During a second step (b1), a compound of formula (III) or a mixture ofcompounds of formula (III) is mixed with the reaction product obtainedduring step (a1), via a stirring system allowing a homogeneouscomposition to be obtained. If necessary, a third step (c1) consists inintroducing a topically acceptable solvent as defined previously to themixture obtained during step (b1), and in continuing the stirring untila uniform composition is obtained.

A third synthetic route consists in subjecting the polyol of formula(A1) or (B1) to a dehydration, in the presence of an acidic catalyticsystem, at a temperature of between 70° C. and 130° C., under partialvacuum, with concomitant removal of the water formed during theintramolecular rearrangement that the polyol undergoes during a firststep (a2); and then in acetalizing the dehydrated polyol thus obtainedby dispersing a reducing sugar in the reaction medium and maintainingthis medium at a temperature of between 80° C. and 130° C., underpartial vacuum, during a second step (b2). The acidic catalytic systemused in this third synthetic route may be identical to that mentionedfor the second route. If necessary, a third step (c2) consists inintroducing a topically acceptable solvent as defined previously intothe mixture obtained during step (b2), and in continuing the stirringuntil a homogeneous composition is obtained.

A fourth synthetic route via trans-acetalization consists in preparingbutylglucoside by reaction between butanol and glucose in the presenceof an acidic catalytic system, at a temperature of between 90° C. and105° C., under partial vacuum, with concomitant removal of the waterformed during the reaction during a first step (a3), the acidiccatalytic system used possibly being identical to that mentioned for thepreceding synthetic routes; adding a polyol of formula (A1) or (B1) tothe reaction medium thus obtained, with removal by distillation undervacuum of the residual butanol, of the butanol formed during thetrans-acetalization reaction, and of any water generated during theintramolecular rearrangement of said polyol during a second step (b3);and, if necessary, a third step (c3) that consists in introducing atopically acceptable solvent as defined previously into the mixtureobtained during step (b3), and in continuing the stirring until ahomogeneous composition is obtained.

According to a third aspect, a subject of the invention as definedpreviously is the use of a compound of formula (I) as definedpreviously, or of a mixture of compounds of formula (I) or the use of acomposition (C) as defined previously, for improving the foamingproperties of a cosmetic, dermocosmetic, dermopharmaceutical orpharmaceutical composition for topical use.

According to a fourth aspect, a subject of the invention is thepreparation of a cleansing and/or foaming formulation for topical use byusing an effective amount of a composition (C) as defined previously.The term “effective amount” denotes a mass proportion of the composition(C) defined previously in the cleansing and/or detergent formulation ofbetween 0.5% and 50%, more particularly between 1% and 30% and mostparticularly between 2% and 10% of the total mass of said formulation.

The compounds of formula (I), the mixtures of compounds of formula (I)and composition (C) as defined previously may be incorporated into anytype of cosmetic, dermocosmetic, dermopharmaceutical or pharmaceuticalformulation intended for topical use, or alternatively into any type ofsupport intended to be placed in contact with the skin (paper, wipe,textile, transdermal device, etc.). The cosmetic formulations fortopical use in which is incorporated an effective amount of compounds offormula (I) or of mixtures of compounds of formula (I), and whichoptionally contain one or more foaming and/or detergent surfactants, oralternatively composition (C) defined previously, may be applied,without preference, to the skin, to the hair, to the scalp and to mucousmembranes, and may especially be in the form of an aqueous or oilysolution, an emulsion or microemulsion of the water-in-oil (W/O) oroil-in-water (O/W) type, a multiple emulsion of water-in-oil-in-water(W/O/W) or oil-in-water-in-oil (O/W/O) type, a gel, a soap or a syndet,a balm, a hydro-dispersion, a cream, a mousse or an aerosol, oralternatively in anhydrous form as a powder. These formulations may beused as cleansing or makeup-removing milks, as cleansing ormakeup-removing lotions, as foaming gels for the face or the body, asshampoos or hair conditioners, or as bubble baths.

In general, these formulations comprise, in addition to the foamingand/or detergent surfactants that may optionally be present therein,excipients and/or active principles usually used in the field offormulations for topical use, in particular cosmetic, dermocosmetic,pharmaceutical or dermopharmaceutical formulations, thickeners, gellingagents, stabilizers, film-forming compounds, solvents and co-solvents,hydrotropic agents, plasticizers, fats, oils, emulsifiers andco-emulsifiers, opacifiers, nacreous agents, overfatting agents,sequestrants, chelating agents, antioxidants, fragrances, preservingagents, conditioning agents, bleaching agents intended for bleachingbodily hair and the skin, sunscreens, mineral fillers or pigments,particles that afford a visual effect or that are intended forencapsulating active agents, exfoliant particles, texture agents,optical brighteners and insect repellents.

As examples of thickening and/or gelling polymers that may be present inthe formulation for which the process that is the subject of the presentinvention is used, mention may be made of:

-   -   homopolymers or copolymers of acrylic acid or of acrylic acid        derivatives, acrylamide homopolymers or copolymers, homopolymers        or copolymers of acrylamide derivatives, homopolymers or        copolymers of acrylamidomethylpropanesulfonic acid, of vinyl        monomer and/or of trimethylaminoethyl acrylate chloride sold        under the names Carbopol™, Ultrez™ 10, Aculyn™, Pemulen™ TR1,        Pemulen™ TR2, Simulgel™ EG, Simulgel™ EPG, Luvigel™ EM, Salcare™        SC91, Salcare™ SC92, Salcare™ SC95, Salcare™ SC96, Flocare™        ET100, Flocare™ ET58, Hispagel™, Sepigel™ 305, Sepigel™ 501,        Sepigel™ 502, Simulgel™ NS, Simulgel™ 800, Simulgel™ A,        Sepiplus™ 250, Sepiplus™ 265, Sepiplus™ 400, Sepinov™ EMT 10,        Novemer™ EC1, Aristoflex™ AVC, Aristoflex™ HBM, Rapithix™ A60,        Rapithix™ A100, Cosmedia™ SP and Stabileze™ 06;    -   hydrocolloids of plant or biosynthetic origin, for example        xanthan gum, karaya gum, carrageenates, alginates or        galactomannans;    -   silicates; cellulose and derivatives thereof; starch and        hydrophilic derivatives thereof; polyurethanes.

As examples of thickening and/or gelling surfactants that may be presentin the formulation for which the process that is the subject of thepresent invention is used, mention may be made of:

-   -   optionally alkoxylated fatty esters of alkylpolyglycosides, and        most particularly ethoxylated esters of methylpolyglucoside such        as PEG 120 methyl glucose trioleate and PEG 120 methyl glucose        dioleate, sold, respectively, under the names Glucamate™ LT and        Glumate™ DOE120;    -   alkoxylated fatty esters such as PEG 150 pentaerythrityl        tetrastearate sold under the name Crothix™ DS53 and PEG 55        propylene glycol oleate sold under the name Antil™ 141;    -   fatty-chain polyalkylene glycol carbamates such as PPG 14        laureth isophoryl dicarbamate sold under the name Elfacos™ T211,        and PPG 14 palmeth 60 hexyl dicarbamate sold under the name        Elfacos™ GT2125.

As examples of emulsifiers that may be present in the formulation forwhich the process that is the subject of the present invention is used,mention may be made of:

-   -   fatty acids, ethoxylated fatty acids, fatty acid esters of        sorbitol, ethoxylated fatty acid esters, polysorbates,        polyglyceryl esters, ethoxylated fatty alcohols, sucrose esters,        alkylpolyglycosides, sulfated and phosphated fatty alcohols or        mixtures of alkylpolyglycosides and of fatty alcohols described        in French patent applications 2 668 080, 2 734 496, 2 756 195, 2        762 317, 2 784 680, 2 784 904, 2 791 565, 2 790 977, 2 807 435,        2 804 432, 2 830 774 and 2 830 445, combinations of emulsifying        surfactants chosen from alkylpolyglycosides, combinations of        alkylpolyglycosides and of fatty alcohols, and polyglycerol or        polyglycol or polyol esters such as the polyglycol or        polyglycerol polyhydroxystearates used in French patent        applications 2 852 257, 2 858 554, 2 820 316 and 2 852 258.

As examples of opacifiers and/or nacreous agents that may be present inthe formulation for which the process that is the subject of the presentinvention is used, mention may be made of sodium or magnesiumpalmitates, stearates or hydroxystearates, ethylene or polyethyleneglycol monostearates or distearates, fatty alcohols, and styrenehomopolymers and copolymers such as the styrene acrylate copolymer soldunder the name Montopol™ OP1 by the company SEPPIC.

As examples of oils that may be present in the formulation for which theprocess that is the subject of the present invention is used, mentionmay be made of:

-   -   mineral oils such as liquid paraffin, liquid petroleum jelly,        isoparaffins or white mineral oils;    -   oils of animal origin, such as squalene or squalane,    -   plant oils, such as phytosqualane, sweet almond oil, coconut        oil, castor oil, jojoba oil, olive oil, rapeseed oil, groundnut        oil, sunflower oil, wheatgerm oil, corn germ oil, soybean oil,        cottonseed oil, alfalfa oil, poppy oil, pumpkin oil, evening        primrose oil, millet oil, barley oil, rye oil, safflower oil,        candlenut oil, passion flower oil, hazelnut oil, palm oil, shea        butter, apricot kernel oil, beauty-leaf oil, sysymbrium oil,        avocado oil, calendula oil and oils obtained from flowers or        vegetables;    -   ethoxylated plant oils;    -   synthetic oils, for instance fatty acid esters such as butyl        myristate, propyl myristate, cetyl myristate, isopropyl        palmitate, butyl stearate, hexadecyl stearate, isopropyl        stearate, octyl stearate, isocetyl stearate, dodecyl oleate,        hexyl laurate, propylene glycol dicaprylate, lanolic acid-based        esters, such as isopropyl lanolate, isocetyl lanolate, fatty        acid monoglycerides, diglycerides and triglycerides, for        instance glyceryl triheptanoate, alkyl benzoates, hydrogenated        oils, poly-α-olefins, polyolefins, for instance polyisobutene,        synthetic isoalkanes such as isohexadecane and isododecane, and        perfluoro oils, and    -   silicone oils, for instance dimethylpoly-siloxanes,        methylphenylpolysiloxanes, silicones modified with amines,        silicones modified with fatty acids, silicones modified with        alcohols, silicones modified with alcohols and fatty acids,        silicones modified with polyether groups, epoxy-modified        silicones, silicones modified with fluoro groups, cyclic        silicones and silicones modified with alkyl groups.

As another fatty material that may be present in the formulation forwhich the process that is the subject of the present invention is used,mention may be made of fatty alcohols or fatty acids; waxes such asbeeswax, carnauba wax, candelilla wax, ouricury wax, Japan wax, corkfiber wax, sugarcane wax, paraffin waxes, lignite waxes,microcrystalline waxes, lanolin wax; ozokerite; polyethylene wax,silicone waxes; plant waxes; fatty alcohols and fatty acids that aresolid at room temperature; glycerides that are solid at roomtemperature.

As examples of active principles that may be present in the formulationfor which the process that is the subject of the present invention isused, mention may be made of compounds with lightening or depigmentingaction, moisturizing action, tensioning action, soothing or relaxingaction, anti-inflammatory action, slimming action, lipolytic action,draining action, detoxifying action, energizing action, decontractingaction, stimulating action, emollient action, neuromodulatory action,protective action, purifying action, sebum-regulating action,hair-loss-counteracting action, anti-ageing action, firming action,restructuring action, free-radical-scavenging action or antioxidantaction; such active principles are, for example, Sepiwhite™ MSH,arbutin, kojic acid, hydroquinone, ellagic acid, vitamin C and itsderivatives, Stay C, magnesium ascorbyl phosphate and its derivatives,ascorbyl glucoside, phytic acid, fruit acids, rucinol or resorcinol,azeleic acid, lipoic acid, Vegewhite™, Gatuline™, Synerlight™,Biowhite™, Phytolight™, Dermalight™, Clariskin™, Melaslow™, Dermawhite™,Ethioline™, Melarest™, Gigawhite™, Albatine™, Lumiskin™, polyphenolextracts, grape extracts, pine extracts, wine extracts, olive extracts,pond extracts, N-acyl proteins, N-acyl peptides, for instance Matrixyl™,N-acylamino acids, partial hydrolysates of N-acyl proteins, amino acids,peptides, total protein hydrolysates, polyols (for instance glycerol,butylene glycol, etc.), milk derivatives, or the various componentsincluded in the composition of NMF (natural moisturizing factor), forexample urea, pyrrolidonecarboxylic acid or derivatives of this acid,amino acids, mineral salts, glucosamines, glycyrrhetinic acid,α-bisabolol, sugars or sugar derivatives, polysaccharides or derivativesthereof, hydroxy acids, for instance lactic acid, vitamins, vitaminderivatives, for instance retinol, vitamin E and its derivatives, traceelements, extracts of rocks or stones, enzymes, coenzymes, for instancecoenzyme Q10, hormones or “hormone-like” substances, for instance PhytoAge™, soybean extracts, for instance Raffermine™, wheat extracts, forinstance Tensine™ or Gliadine™, plant extracts such as tannin-rich plantextracts, isoflavone-rich plant extracts or terpene-rich plant extracts,freshwater or saltwater algal extracts, marine extracts in general,including coral extracts, essential waxes, bacterial extracts, minerals,for instance the range of Givobio™ products, calcium, magnesium, copper,cobalt, zinc, lithium or manganese derivatives, silver or gold salts,lipids in general, lipids such as ceramides or phospholipids, activeagents with slimming or lipolytic action, for instance caffeine orderivatives thereof, calcium and derivatives thereof, and Lipaslim™,active agents that improve the capillary circulation of the skin, forexample venotonic agents, water retention-reducing active agents, activeagents for decongesting purposes such as ginkgo biloba, ivy, commonhorse chestnut, bamboo, ruscus, centella asiatica, fucus, rosemary orsage, active agents with antimicrobial activity or a purifying action ongreasy skin, for instance Lipacide™ CBG, Lipacide™ UG, Sepicontrol™ A5,copper or zinc derivatives, Octopirox™ or Sensiva™ SC50, active agentswith energizing or stimulating properties, for instance Sepitonic™ M3 orPhysiogenyl™, panthenol and derivatives thereof, for instance Sepicap™MP, anti-ageing active agents, for instance Sepilift™ DPHP, Lipacide™PVB, Sepivinol™, Sepivital™, Manoliva™ and Phyto-Age™, moisturizingactive agents, for instance Sepicalm™ S, Sepicalm™ VG and Lipacide™DPHP, photoageing-counteracting active agents, active agents forprotecting the integrity of the dermo-epidermal junction, active agentsfor increasing the synthesis of components of the extracellular matrix,for example collagen, elastins, glycosaminoglycans, active agents thatact favorably on chemical cellular communication, for instancecytokines, or on physical cellular communication, for instanceintegrins, active agents that create a “heating” sensation on the skin,for instance activators of the capillary circulation of the skin (forexample nicotinates) or products that create a sensation of “freshness”on the skin (for example menthol and derivatives thereof).

As sunscreens that may be present in the formulation for which theprocess that is the subject of the present invention is used, mentionmay be made of all the agents featured in Cosmetic Directive 76/768/EECamended appendix VII.

The examples that follow illustrate the invention without, however,limiting it.

A)—Preparation of the Compounds of Formula (I) or of Mixtures ofCompounds of Formula (I), and of the Compositions According to theInvention EXAMPLE 1 Composition (C1) Constituted ofXylitylpolyglucosides, Sodium Lauryl Ether (2.2 EO) Sulfate and Xylitol

703.0 g of xylitol are placed in a jacketed glass reactor, in whichcirculates a heat-exchange fluid, and which is equipped with anefficient stirrer. The xylitol is melted at a temperature of 135° C. andthe viscous paste thus obtained is cooled to 115° C. Glucose is thengradually added to the reaction medium to allow its uniform dispersion.An acidic catalytic system constituted of 1.29 g of 96% sulfuric acid isadded to the mixture thus obtained. The reaction medium is placed undera partial vacuum of 90×10² Pa (90 mbar) to 45×10² Pa (45 mbar) andmaintained at a temperature of 100° C.-105° C. for a duration of 4 hours30 minutes, with removal of the water formed by means of distillationapparatus. The reaction medium is then cooled to 95° C.-100° C. andneutralized by adding 5 g of 30% sodium hydroxide, to bring the pH of a1% solution of this mixture to a value of 5.0. The characteristics ofthe intermediate mixture thus obtained are as follows:

-   -   aspect (visual): orange wax at room temperature;    -   pH of a 1% solution: 5.0;    -   residual xylitol: 56 mass %;    -   residual glucose: <1 mass %;    -   xylitylpolyglucosides: 38 mass %.

15.86 g of the intermediate mixture obtained previously and 572.9 g ofsodium lauryl ether (2.2 EO) sulfate at 28% in water are mixed togetherat 50° C. in a jacketed glass reactor, in which circulates aheat-exchange fluid, and which is equipped with an efficient stirrer.

After obtaining a homogeneous mixture, composition (C1) comprises, per100 mass % of its dry matter, 91% sodium lauryl ether (2.2 EO) sulfate,4% xylitylpolyglucoside and 5% xylitol.

COMPARATIVE EXAMPLE 1 Sodium Lauryl Ether (2.2 EO) Sulfate (T1) EXAMPLE2 Composition (C2) Constituted of Xylitylpolyglucosides,n-decyl/n-dodecyl Polyglucosides and Xylitol

The xylitylpolyglucosides are prepared according to the processdescribed in Example 1 until an intermediate mixture comprising, per100% of its mass, 37.2 mass % of xylitylpolyglucosides, 55.8 mass % ofxylitol and a mass proportion of residual glucose of less than 1% isobtained. 20 g of the intermediate mixture obtained previously and 113.3g of a mixture of n-decylpolyglucosides and of n-dodecylpolyglucosides(C10/C12=85/15) as a 55% solution are mixed together at 50° C. in ajacketed glass reactor, in which circulates a heat-exchange fluid, andwhich is equipped with an efficient stirrer. After obtaining a uniformmixture, composition (C2) comprises, per 100 mass % of its dry matter,77% n-decylpolyglucosides/n-dodecylpolyglucosides, 9%xylitylpolyglucosides and 14% xylitol.

COMPARATIVE EXAMPLE 2 Composition (T2) Constituted of n-decyl/n-dodecylPolyglucosides and Xylitol

A 55% solution of n-decylpolyglucosides and of n-dodecylpolyglucosides(C10/C12=85/15) is placed in a beaker at room temperature. The medium isstirred with a magnetic bar coupled to a magnetic stirrer and xylitol isgradually introduced in proportions allowing a composition containing 77mass % of solids of n-decylpolyglucosides/n-dodecylpolyglucosides and 23mass % of xylitol to be obtained.

EXAMPLE 3 Composition (C3) Constituted of Xylitylpolyglucosides,n-octyl/n-decyl Polyglucosides and Xylitol

The xylitylpolyglucosides are prepared according to the processdescribed in Example 1, until an intermediate mixture comprising, per100% of its mass, 37.2 mass % of xylitylpolyglucosides, 55.8 mass % ofxylitol and a mass proportion of residual glucose of less than 1% isobtained. 20 g of the intermediate mixture obtained previously and 103.8g of a mixture of n-octylpolyglucosides and of n-decylpolyglucosides(C8/C10=50/50) as a 60% solution are mixed together at 50° C. in ajacketed glass reactor, in which circulates a heat-exchange fluid, andwhich is equipped with an efficient stirrer. After obtaining ahomogeneous mixture, the mass composition of composition (C3) comprises,per 100% of its dry matter, 77%n-octylpolyglucosides/n-decylpolyglucosides, 9% xylitylpolyglucosidesand 14% xylitol.

COMPARATIVE EXAMPLE 3 Solution Containing 55% Dry Matter ofn-decylpolyglucosides/n-dodecylpolyglucosides (T3) EXAMPLE 4 Composition(C4) Constituted by Xylitylpolyglucosides, n-octyl/n-decylPolyglucosides and Xylitol

The xylitylpolyglucosides are prepared according to the processdescribed in Example 1, until an intermediate mixture comprising, per100% of its mass, 37.2 mass % of xylitylpolyglucosides, 55.8 mass % ofxylitol and a mass proportion of residual glucose of less than 1% isobtained. 20 g of the intermediate mixture obtained previously and 62.1g of a mixture of n-octylpolyglucosides and of n-decylpolyglucosides asa 60% solution are mixed together at 50° C. in a jacketed glass reactor,in which circulates a heat-exchange fluid, and which is equipped with anefficient stirrer. After obtaining a homogeneous mixture, composition(C4) comprises, per 100% of its dry matter, 68%n-octylpolyglucosides/n-decylpolyglucosides, 7% xylitylpolyglucosidesand 25% xylitol.

COMPARATIVE EXAMPLE 4 Solution Containing 55% Dry Matter ofn-octylpolyglucosides/n-decylpolyglucosides (T4) EXAMPLE 5 Composition(C5) Constituted by Diglyceryl-Polyxylosides, n-octyl/n-decylPolyglucosides and Diglycerol

650.0 g of diglycerol are placed in a jacketed glass reactor, in whichcirculates a heat-exchange fluid, and which is equipped with anefficient stirrer. The diglycerol is brought to a temperature of about100° C. 1117.5 g of xylose are then gradually added to the reactionmedium to allow its uniform dispersion. An acidic catalytic systemconstituted of 0.51 g of 98% sulfuric acid is added to the mixture thusobtained. The reaction medium is placed under a partial vacuum of 30×10²Pa (30 mbar) and maintained at a temperature of 100° C.-105° C. for aduration of 4 hours, with removal of the water formed by means ofdistillation apparatus. The reaction medium is then cooled to 95°C.-100° C. and neutralized by adding 30% sodium hydroxide, to bring thepH of a 1% solution of this mixture to a value of about 7.0. Thecharacteristics of the intermediate mixture thus obtained are asfollows:

-   -   aspect (visual): clear liquid;    -   pH of a 1% solution: 6.8;    -   residual diglycerol: 68.1%;    -   residual xylose: <1%;    -   diglycerylpolyxylosides: 27.7%.

20 g of the intermediate mixture obtained previously and 133.3 g of amixture of n-octylpolyglucosides and n-decylpolyglucosides as a 60%solution are mixed together at 50° C. in a jacketed glass reactor, inwhich circulates a heat-exchange fluid, and which is equipped with anefficient stirrer. After obtaining a uniform mixture, composition (C5)comprises, per 100% of its dry matter, 80%n-octylpolyglucosides/n-decylpoly-glucosides, 6% diglycerylpolyxylosidesand 14% diglycerol.

EXAMPLE 6 Composition (C6) Constituted by Diglycerylpolyglucosides,n-dodecyl/n-tetradecyl/n-hexadecyl Polyglucosides and Diglycerol

The process described in Example 5 is performed to prepare thediglycerylpolyglucosides, replacing the xylose with glucose and keepingthe same reducing sugar/diglycerol mole ratio equal to 1/5. Thecharacteristics of the intermediate mixture thus obtained are asfollows:

-   -   aspect (visual): clear liquid;    -   pH of a 1% solution: 6.8;    -   residual diglycerol: 67.2%;    -   residual glucose: <1%;    -   diglycerylpolyglucosides: 24.7%.

20 g of the intermediate mixture obtained previously and 120 g of amixture of n-decylpolyglucosides, n-dodecylpolyglucosides,n-tetradecylpolyglucosides and n-hexadecylpolyglucosides sold under thename Plantacare™ 1200 UP are mixed together at 50° C. in a jacketedglass reactor, in which circulates a heat-exchange fluid, and which isequipped with an efficient stirrer. After obtaining a uniform mixture,composition (C6) comprises, per 100% of its dry matter, 75% of a mixtureof n-decylpolyglucosides, n-dodecylpolyglucosides,n-tetradecylpolyglucosides and n-hexadecylpolyglucosides, 8%diglycerylpolyglucosides and 17% diglycerol.

Summary Table

Table 1 below summarizes the mass compositions, as dry matter, ofvarious compositions prepared and intended to be used in tests ofdemonstration of the foaming properties.

TABLE 1 Composition (as mass %) C1 T1 C2 T2 C3 T3 C4 T4 C5 C6 Sodiumlauryl 91 100 0 0 0 0 0 0 0 0 ether (2.2 EO) sulfate Xylityl 4 0 9 0 9 07 0 0 0 polyglucosides Xylitol 5 0 14 23 14 0 25 0 0 0 Diglyceryl 0 0 00 0 0 0 0 6 0 polyxylosides Diglyceryl 0 0 0 0 0 0 0 0 0 8polyglucosides Diglycerol 0 0 0 0 0 0 0 0 14 17 n-Octyl/n-decyl 0 0 0 077 0 68 100 80 0 polyglucosides n-Decyl/n- 0 0 77 77 0 100 0 0 0 0dodecyl polyglucosides n-Decyl/n- 0 0 0 0 0 0 0 0 0 75 dodecyl/n-tetradecyl/n- hexadecyl polyglucosides

B—Demonstration of the Foaming Properties of Formulations ComprisingCompounds of Formula (I) or Mixtures of Compounds of Formula (I), and ofthe Compositions (C) According to the Invention

The demonstration of the foaming properties of formulations comprisingcompounds of formula (I) or mixtures of compounds of formula (I), and ofthe compositions (C) defined previously forming the subject of theinvention, may be performed by evaluating the foaming power or byevaluating the sensory characteristics that the foam formed gives tousers during the washing or cleansing operation.

B.1—Demonstration of the Foaming Power B.1.1—Principle of the Ross-MilesMethod for Evaluating the Foaming Power

The foaming power is determined according to the Ross-Miles protocolderived from standard ISO 696 and AFNOR NFT 73-404 and described inparagraph B1.2, diluting the cleansing bases and the compositionsprepared previously tenfold, so as to represent the real conditions offoam creation during the use of a shampoo, for example.

The tenfold dilution of the compositions and of the formulations to betested is performed in the presence of 0.25% of a greasy soiling (areconstituted sebum) with a demineralized water enriched with 3 millimolof calcium ions, which corresponds to the preparation of a water with acalcium hardness of 30° according to standard NFT 73-047.

The method consists in measuring the volume of foam obtained afterdropping, from a height of 450 mm, 500 cm³ of a solution of compositionor of formulation to be tested, onto a liquid surface of the samesolution.

B.1.2—Experimental Protocol

a) Preparation of a Stock Solution (S)

A stock solution is prepared for each test. For the surfactantcompositions or formulations to be tested, prepare 100 g of a stocksolution (S) with a 10% titer of active material or of solids, dilutedwith demineralized water enriched with 3 mmol of calcium ions, whichcorresponds to the preparation of a water with a calcium hardness of 30°according to standard NFT 73-047.

b) Preparation of the Soiling

In the case of determining the foam height in the presence of artificialsoiling, the amount of soiling (0.25%, i.e. 1.75 g per 700 g of finalsolution) and the amount of solution S (i.e. 70 g per 700 g of finalsolution) required to perform the measurements are weighed outbeforehand. The mixture is melted on a water bath preheated to 70° C.,for 3 minutes, while stirring with a spatula.

c) Preparation of the Test Solution

The premelted mixture [S+soiling] is diluted tenfold with demineralizedwater enriched with 3 mmol of calcium ions. The service life of the testsolutions is a maximum of 1 hour from the moment at which the finaldilution was prepared. The final test solution is then preheated on awater bath at 48° C. for a minimum of 1 hour, and then maintainedthermostatically for 30 minutes to reach a temperature of 40° C.±1° C.

d) Measurement

50 cm³ of the test solution are placed in a 50 cm³ measuring cylinder,running the liquid down the walls to avoid any formation of foam. Adropping funnel equipped at its end with a steel tip, such that theheight between the surface of the solution contained in the measuringcylinder and the end of the steel tip is 450 mm, is placed a fixedheight above the measuring cylinder. About 100 cm³ of the test solutionare introduced into the dropping funnel, by running down the walls, andthe level is adjusted by pouring up to the graduation mark, thuseliminating the air present in the eye of the tap.

500 cm³ of test solution are then introduced into the dropping funnel,by running down the walls. The dropping funnel is placed on its supportand the tap is opened so as to allow the solution to flow in a singleportion into the measuring cylinder at a maximum flow rate. The tap isclosed when the solution reaches the graduation mark, and thechronometer is then simultaneously started. The height of foamimmediately formed on starting the chronometer, and then the height offoam at 30 seconds, at 3 minutes and at 5 minutes, are measured in cm.The foam height is measured between the foam/liquid horizontal interfaceand the base of the foam/air interface.

B.1.3—Expressing the Results

The result of the volume of foam at 30 seconds is expressed in cm³ bymultiplying the height measured at 30 seconds in cm by the cross sectionof the measuring cylinder (30.2 cm² or 28.3 cm² depending on the model).The stability of the foam after 5 minutes, measured as a percentage, iscalculated according to the formula:[(volume of foam at 30 s−volume of foam at 5 min)/volume of foam at 30s]×100.

B.1.4—Influence of the Compounds of Formula (I) or of the Mixtures ofCompounds of Formula (I) on the Foaming Power of Formulations ComprisingCompounds of Formula (II) B.1.4.1—Results Obtained

TABLE 2 evaluation of the foaming power of a solution containing acompound of formula (II) and a mixture of compounds of formula (I)(composition C1) and of a solution containing a compound of formula (II)(T1). Foaming power (C1) T1 Volume of foam at 30 seconds (cm³) 350 317Foam stability at 5 minutes (%) 94% 83%

B.1.4.2—Analysis of the Results

The results are considered satisfactory when the test solution shows avolume of foam at 30 seconds of greater than or equal to 300 cm³ and afoam stability at 5 minutes of greater than or equal to 90%. ComparativeExample 1 shows that a solution comprising a compound of formula (II),tested under the conditions described above, is characterized by thegeneration of an abundant foam at 30 seconds (317 cm³) and by astability of 83% after 5 minutes. Use of the process according to theinvention for preparing composition (C1) makes it possible to achieveboth a greater volume of foam after seconds and also a substantiallygreater foam stability at 5 minutes (94% for composition (C1) and 83%for (T1)). Use of the process according to the invention thus makes itpossible to improve the foaming power of compounds of formula (II).

B.2—Demonstration of the Sensory Properties

Among the characteristics that will also be taken into consideration forassessing the quality of a foam formed by a foaming surfactant solution,by a foaming composition and by a foaming formulation, are the sensorycharacteristics that the foam affords to the user, and which concern theassessment of the softness of the foam formed, the capacity to alloweasy sliding of the hands during washing (the “slipperiness”), the easeof rinsing after the washing operation, and the stability of the foam ondilution with washing water during this final operation. Thesecharacteristics are determined experimentally by a representative panelof duly trained users, according to the protocol detailed in paragraphB.2.2.

B.2.1—Principle of the Method

The sensory properties of the foam generated by the foaming compositionsare evaluated during a hand washing operation by a panel of 10individuals duly trained for this evaluation, who classify on a scaleranging from 0 to 10: the softness index of the foam, which makes itpossible to evaluate the softness sensation experienced by the user; theslipperiness index of the foam, which makes it possible to evaluate theease with which the hands slide over each other during the phase ofrubbing of the hands in the washing operation; the stability index ofthe foam on dilution, which makes it possible to evaluate the stabilityof the foam contained in the hand after the phase of rubbing the handsfollowed by the addition of 2 cm³ of water; the rinseability index ofthe foam, which makes it possible to evaluate the ease of rinsing of thehands with water after the operation of rubbing the hands with thecleansing product in the form of foam.

B.2.2—Experimental Protocol

To take reproducible measurements, the solutions were conditioned inbottles equipped with a metering foam pump, which directly expels theproduct in the form of foam onto the hands with a fixed amount of testproduct. The product contained in the bottle is applied directly to oneof the hands, which has been moistened beforehand, by pressing twicesuccessively on the foam pump of the bottle. On the moistened handcontaining the product from the bottle, the experimenter rubs the otherhand out flat for 5 seconds, and then rubs the hands clasped togetherfor a further 5 seconds. The foam is collected together in a single handto be evaluated by the experimenter, who notes the softness index andthe slipperiness index of the foam. 2 cm³ of water are then added from agraduated pipette onto the hand containing the collected foam, and theexperimenter notes the stability index of the foam on dilution. Theexperimenter then rinses his hands under a tap of cold water andevaluates the rinseability of the foam.

B.2.3—Expressing the Results

A softness index of 0 is attributed to a very coarse foam and a softnessindex of 10 is attributed to a very soft foam. A foam slipperiness indexof 0 is attributed to a foam that sticks on the hands and a foamslipperiness index of 10 is attributed to a foam that is very slipperyon the hands. A stability index of the foam on dilution of 0 isattributed to a foam that collapses when the 2 cm³ of water are addedand a stability index of the foam on dilution of 10 is attributed to afoam that is perfectly maintained when the 2 cm³ of water are added. Arinseability index of 0 is attributed for a hand rinsing considered asbeing very difficult and a rinseability index of 10 is attributed for ahand rinsing considered as being very easy. For each index, theevaluations made by each of the 10 experimenters are noted and thearithmetic mean of each index is then calculated.

B.2.4—Sensory Properties of the Cleansing and/or Detergent FormulationsObtained by Using the Process According to the Invention and theCompositions According to the Invention B.2.4.1—Results Obtained

TABLE 3 evaluation of the sensory properties Sensory property indices C1T1 C2 T2 T3 C3 C4 T4 Softness 8 7 7.7 5.2 4.0 5.5 6.0 3.0 Slipperiness 65.5 7.4 4.0 3.4 5.5 6.5 3.0 Foam stability 5 3 6.8 5.5 4.5 5.4 6.0 4.0after dilution Rinseability 5.1 5.3 6.7 6.0 7.3 6.9 7.0 7.1

B.2.4.2—Analysis of the Results

The results are considered as being satisfactory when one or more of thesensory property indices for the test formulation or the testcomposition shows a significant improvement, without significantlyreducing one or more of the other indices; said indices takenindividually should show a value of greater than or equal to 5.0. Theyreveal an improvement in one or other of the sensory properties inducedby the compositions according to the invention compared with those ofthe prior art.

C)—Formulations

In the following formulations, the percentages are expressed by weightof the formulation.

C.1 Foaming Facial Gel

Formula

A 28% sodium lauryl ether (2.2 EO) sulfate 5.9% Water qs 100%   BComposition (C5) according to the invention 5.0% Montaline ™ C40 5.0%Sepitonic ™ M³ 1.0% Fragrance 0.1% Kathon ™ CG 0.08%  C Lactic acid0.15%  Sodium chloride 0.8% D Dye 0.05%  E Sodium chloride qs

Procedure

Prepare phase A in a fume cupboard. Mix together the ingredients ofphase B, homogenizing after each addition. Next, pour A into B. Add Cand then D. Adjust the viscosity if necessary by adding E (1.5% max.).

C.2 Bubble Bath for Children

Formula

A Oronal ™ LCG 10.00% Composition (C2) according to the invention 13.00%Fragrance 00.10% Sepicide ™ HB 00.50% B Water 20.00% Capigel ™ 98 04.50%C Water qs 100%  Sepicide ™ CI 00.30% Dye qs Sodium hydroxide qs

Procedure

Mix the Oronal™ LCG with the amphoteric surfactant, the fragrance andthe preserving agent. Dilute the Capigel™ in a portion of water and addit to the surfactants, then add the rest of the water. Add the Sepicide™CI and the dye, and then adjust the pH to about 7.2.

C.3 Liquid Soap for the Hands

Formula

A Composition (C1) 10.00% Amonyl ™ 675SB 10.00% Fragrance 00.30%Sepicide ™ HB 00.50% B Water qs 100%  Sepicide ™ CI 00.30% Sodiumchloride qs

Procedure

Mix together the ingredients of phase A and then add phase B.

C.4 Concentrated Purifying Lotion

Formula

A Water 20.00% Lipacide ™ UGB  1.00% Tromethamine  0.75% B PEG 120methyl glucose dioleate  5.00% Water qs 100%  Composition (C6) accordingto the invention 29.00% Glycerol  5.00% C Lactic acid qs pH 4

Procedure

Dissolve the Lipacide™ UGB in part of the water heated to 80° C. andthen add the tromethamine: this phase should be totally clear. Melt thePEG 120 methyl glucose dioleate in the rest of the water preheated to80° C. Add to this phase the glycerol and the composition of theinvention: this phase is also totally clear. Mix together the twophases, allow to cool and readjust the pH to the desired value.

C.5 Cleansing Facial Foam

Formula

A Proteol ™ Oat   30% Composition (C3) according to the invention 10.00%Sepicide ™ HB 00.50% Fragrance 00.20% B Water qs 100%  Sepicide ™ CI00.30% Sepitonic ™ M3 01.00% Tromethamine qs Dye qs

Procedure

Dissolve the fragrance and the preserving agent in the mixture ofsurfactants (A). Add the water and then the other ingredientssuccessively.

C.6 Anti-Stress Shampoo

Formula

A Composition (C1) 20.00% Sepicide ™ HB  0.50% Sepicide ™ CI  0.30%Fragrance  0.30% Water qs 100%  Sepicap ™ MP  1.00% B Water 10.00%Capigel ™ 98  3.00% Sodium hydroxide qs pH 7.2 Dye qs

Procedure

Mix together the ingredients A and then add the prediluted Capigel.Neutralize.

C.7 Cleansing Wipes

Formula

A Composition (C6) 02.00% Aquaxyl ™ 01.00% B Sepicide ™ HB₂ 00.50%Fragrance 00.05% Hexylene glycol 10.00% C Water qs 100% 

Procedure

Mix together the ingredients of phase B until clear and then add thisphase to phase A. Add C.

C.8 Relaxing Bath Oil

Formula

Cedar wood extract 10.00% Composition (C5) 66.00% Glycerol 24.00%

Procedure

Mix together the essential oil and the composition of the inventionuntil clear. Next, add the glycerol.

C.9 Gentle Cleansing Product with Jojoba Oil

A Montanov ™ S 3.0% PEG-120 methyl glucose dioleate 2.0% B Jojoba oil0.5% Dimethicone and laureth-23 and laureth-4 and 2.0% salicylic acid CWater 30.0%  Glycerol 3.0% Polyquaternium ™ 10 0.7% D Somepon ™ T25 4.5%Composition (C6) 30.0%  Water 5.0% Sepicide ™ CI 0.2% Sepicide ™ HB 0.3%Fragrance 0.1% E Water qs 100%    Capigel ™ 98 2.0% Sodium hydroxide qspH 7

Procedure

Disperse the Polyquaternium™ 10 of phase C in the water+glycerolmixture. Heat to 70° C. and add the ingredients of A and then of B.Emulsify. Start cooling. At 60° C., add the surfactants one by one (D).At 30° C., add the prediluted Capigel™ (E). Finally, neutralize withsodium hydroxide.

C.10 Antibacterial Liquid Soap

Composition (C6) 15.00% Chlorhexidine digluconate 00.20% Oramide ™ DL200 AF 03.00% Water qs 100%   Fragrance 00.05% Dye qs Sodium chloride qs

Procedure

Add together and mix the constituents in the indicated order.

C.11 Conditioning Shampoo

A Cetyltrimethylammonium chloride 03.50% Composition (C5) 25.00%Dimethicone copolyol 01.00% Fragrance 00.50% Amonyl ™ 380BA 11.00%Kathon ™ CG  0.08% B Polyquaternium ™ 10 00.30% Lactic acid qs Water qs100%  Dye qs Lactic acid qs pH 6

Procedure

Prepare separately phase B: mix until clear. Carefully mix in theingredients in the indicated order.

C.12 Bath Powder

A Micropearl ™ M  5.00% Mica 72.00% Pigment  3.00% B Rosmarinusofficinalis (rosemary) leaf 10.00% extract Composition (C5) 10.00%

Procedure

Grind the powders of phase A. Dissolve the essential oil withcomposition 4 according to the invention (B) and slowly introduce thisphase B into the ground material, leaving the mixture to stir for 6minutes after the end of introduction of the liquid phase.

The characteristics of the products used in the preceding examples areas follows:

Sepitonic™ M3, a mixture of magnesium aspartate, zinc gluconate andcopper gluconate, is an energizing active agent sold by the companySEPPIC.

Polyquaternium™ 10 is a quaternary ammonium salt ofhydroxyethylcellulose, sold by the company Amerchol under the name UcarePolymer™ JR-400.

Kathon™ CG, a mixture of methylchloroisothiazolinone and ofmethylisothiazolinone, is a preserving agent sold by the company Rohm &Haas.

Oronal™ LCG, a mixture of PEG-40 glyceryl cocoate and of sodium cocethsulfate, is a foaming agent sold by the company SEPPIC.

Amonyl™ 675SB is a cocamidopropyl hydroxy sultaine, sold by the companySEPPIC.

Sepicide™ HB, a mixture of phenoxyethanol, methyl paraben, ethylparaben, propyl paraben and butyl paraben, is a preserving agent sold bythe company SEPPIC.

Capigel™ 98 is an acrylate copolymer sold by the company SEPPIC.

Sepicide™ CI, imidazolineurea, is a preserving agent sold by the companySEPPIC.

Sepicide™ HB2, a mixture of phenoxyethanol, methyl paraben, ethylparaben, propyl paraben, butyl paraben and isobutyl paraben, is apreserving agent sold by the company SEPPIC.

Proteol™ Oat is a mixture of N-lauryl amino acids obtained by totalhydrolysis of oat protein as described in WO 94/26694 and sold by thecompany SEPPIC.

Montaline™ C40 is a salt of monoethanolamine cocamidopropyl betainamidechloride.

Montanov™ S (C12-C18 alcohols and cocoglucosides) is a self-emulsifyingcomposition such as those described in EP 0 729 382, sold by the companySEPPIC.

Sepicap™ MP is a mixture of N-cocoyl amino acids and of the potassiumsalt of dimethicone PEG-7 panthenyl phosphate, sold by the companySEPPIC.

Aquaxyl™ is a moisturizing active agent comprising a mixture ofxylitylpolyglucosides, anhydroxylitol and xylitol, sold by the companySEPPIC.

Somepon™ T25 is a sodium methyl cocoyl taurate, sold by the companySEPPIC.

Lipacide™ UGB is undecylenoyl lysine, sold by the company SEPPIC.

Oramide™ DL 200 AF is a diethanolamide cocamide sold by the companySEPPIC.

Amonyl™ 380BA is a cocamidopropyl betaine sold by the company SEPPIC.

Micropearl™ M is a crosslinked polymethyl methacrylate polymer in powderform, which is used as a texture modifier.

What is claimed is:
 1. A method for improving the foaming properties ofat least one of a cleansing or detergent formulation for topical usehaving at least one of a foaming or detergent surfactant, the methodcomprising: incorporating into said formulation an effective amount of acompound of formula (I):R₁—O-(G)_(x)-H  (I) wherein, x represents a decimal number between 1 and5, G represents a reducing sugar residue, and R₁ represents a monovalentradical of formula (A): —CH₂—(CHOH)_(n)—CH₂—OH (A), wherein n is aninteger equal to 2, 3 or 4, or R₁ represents a monovalent radical offormula (B): —(CH₂—CHOH—CH₂—O)_(m)H (B), wherein m is an integer equalto 1, 2 or 3, or a mixture of compounds of formula (I).
 2. The methodaccording to claim 1, wherein G represents a reducing sugar residueselected from the group consisting of: glucose, dextrose, sucrose,fructose, idose, gulose, galactose, maltose, isomaltose, maltotriose,lactose, cellobiose, mannose, ribose, xylose, arabinose, lyxose, allose,altrose, dextran and talose.
 3. The method according to claim 1, whereinG represents a reducing sugar residue selected from the group consistingof: glucose, xylose and arabinose.
 4. The method according to claim 1,wherein the at least one of a foaming or detergent surfactant is acompound of formula (II):R₂—[O—(CH₂—CH₂—O)_(p)SO₃]_(r)X  (II) wherein, R₂ represents a saturatedor unsaturated, linear or branched aliphatic hydrocarbon-based radicalcontaining from 6 to 22 carbon atoms, p represents a decimal numberbetween 1 and 10, r is an integer equal to 1 or 2, and X represents acation of an alkali metal or of an alkaline-earth metal, ammonium ion,hydroxyethylammonium ion or tris(hydroxyethyl)ammonium ion, or a mixtureof compounds of formula (II).
 5. The method according to claim 1,wherein the at least one of a foaming or detergent surfactant is acompound of formula (III):R₃—O—(S)_(y)—H  (III) wherein, y represents a decimal number between 1and 5, S represents a reducing sugar residue, and R₃ represents a linearor branched, saturated or unsaturated alkyl radical containing from 8 to16 carbon atoms.
 6. The method according to claim 1, wherein a massratio of compound of formula (I) to foaming and/or detergent surfactantpresent in said formulation for topical use is between 1/30 and 10/1. 7.The method according to claim 4, wherein a mass ratio of compound offormula (I) to foaming and/or detergent surfactant present in saidformulation for topical use is between 1/30 and 10/1.
 8. The methodaccording to claim 5, wherein the mass ratio of compound of formula (I)to foaming and/or detergent surfactant present in said formulation fortopical use is between 1/30 and 10/1.
 9. The method according to claim4, wherein p represents a decimal number between 2 and
 4. 10. The methodaccording to claim 1, wherein x is a number between 1.05 and
 2. 11. Themethod according to claim 1, wherein the effective amount of thecompound of formula (I) is incorporated into the formulation in anamount of 0.1% to 20% by mass of total formulation.
 12. The methodaccording to claim 1, wherein the effective amount of the compound offormula (I) is incorporated into the formulation in an amount 1% to 5%by mass of total formulation.
 13. The method according to claim 4,wherein X is sodium, magnesium or ammonium.
 14. The method according toclaim 5, wherein y is a number between 1.05 and
 2. 15. The methodaccording to claim 5, wherein R₃ is an n-octyl radical, n-decyl radical,n-dodecyl radical, n-tetradecyl radical or n-hexadecyl radical.